Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)

The synthesis of a germylidenide anion by the C-C bond activation of a bis(germylene) is described. The reaction of the 2,6-bis(imino)phenyl bromide 1 with nBuLi, followed by reacting with GeCl2·dioxane, afforded the chlorogermylene [LGeCl] (2, L = 2,6-(HCNtBu)2C6H3). It was then reacted with 1 equi...

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Main Authors:	Seow, Celestine, Xi, Hong-Wei, Li, Yongxin, So, Cheuk-Wai
Other Authors:	School of Materials Science & Engineering
Format:	Article
Language:	English
Published:	2020
Subjects:	Engineering::Materials Dianion Aromaticity
Online Access:	https://hdl.handle.net/10356/138205
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Institution:	Nanyang Technological University
Language:	English

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spelling	sg-ntu-dr.10356-1382052023-02-28T19:41:35Z Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene) Seow, Celestine Xi, Hong-Wei Li, Yongxin So, Cheuk-Wai School of Materials Science & Engineering School of Physical and Mathematical Sciences Engineering::Materials Dianion Aromaticity The synthesis of a germylidenide anion by the C-C bond activation of a bis(germylene) is described. The reaction of the 2,6-bis(imino)phenyl bromide 1 with nBuLi, followed by reacting with GeCl2·dioxane, afforded the chlorogermylene [LGeCl] (2, L = 2,6-(HCNtBu)2C6H3). It was then reacted with 1 equiv of lithium in tetrahydrofuran (THF), which proceeded through the reduction of the imine skeleton, along with the C-C bond formation, to afford the bis(germylene) [2-(HC-NtBu)-6-(HC-NtBu)C6H3Ge:]2 (3). It was further reacted with 2 equiv of lithium in THF, which proceeded through the reduction of the germanium(II) centers, followed by the homolytic cleavage of the C-C bond, to form the lithium germylidenide [LGeLi]2 (4). Compounds 2-4 were characterized by NMR spectroscopy and X-ray crystallography. Their bonding natures were also investigated by theoretical studies. Accepted version 2020-04-29T02:34:45Z 2020-04-29T02:34:45Z 2016 Journal Article Seow, C., Xi, H.-W., Li, Y., & So, C.-W. (2016). Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene). Organometallics, 35(8), 1060-1063. doi:10.1021/acs.organomet.5b01001 0276-7333 https://hdl.handle.net/10356/138205 10.1021/acs.organomet.5b01001 2-s2.0-84969180628 8 35 1060 1063 en Organometallics This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.organomet.5b01001 application/pdf
institution	Nanyang Technological University
building	NTU Library
continent	Asia
country	Singapore Singapore
content_provider	NTU Library
collection	DR-NTU
language	English
topic	Engineering::Materials Dianion Aromaticity
spellingShingle	Engineering::Materials Dianion Aromaticity Seow, Celestine Xi, Hong-Wei Li, Yongxin So, Cheuk-Wai Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)
description	The synthesis of a germylidenide anion by the C-C bond activation of a bis(germylene) is described. The reaction of the 2,6-bis(imino)phenyl bromide 1 with nBuLi, followed by reacting with GeCl2·dioxane, afforded the chlorogermylene [LGeCl] (2, L = 2,6-(HCNtBu)2C6H3). It was then reacted with 1 equiv of lithium in tetrahydrofuran (THF), which proceeded through the reduction of the imine skeleton, along with the C-C bond formation, to afford the bis(germylene) [2-(HC-NtBu)-6-(HC-NtBu)C6H3Ge:]2 (3). It was further reacted with 2 equiv of lithium in THF, which proceeded through the reduction of the germanium(II) centers, followed by the homolytic cleavage of the C-C bond, to form the lithium germylidenide [LGeLi]2 (4). Compounds 2-4 were characterized by NMR spectroscopy and X-ray crystallography. Their bonding natures were also investigated by theoretical studies.
author2	School of Materials Science & Engineering
author_facet	School of Materials Science & Engineering Seow, Celestine Xi, Hong-Wei Li, Yongxin So, Cheuk-Wai
format	Article
author	Seow, Celestine Xi, Hong-Wei Li, Yongxin So, Cheuk-Wai
author_sort	Seow, Celestine
title	Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)
title_short	Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)
title_full	Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)
title_fullStr	Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)
title_full_unstemmed	Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)
title_sort	synthesis of a germylidenide anion from the c-c bond activation of a bis(germylene)
publishDate	2020
url	https://hdl.handle.net/10356/138205
_version_	1759858295307239424

Synthesis of a germylidenide anion from the C-C bond activation of a bis(germylene)

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